


Our Boy Tonight

by Dangerousnotbroken



Category: Supernatural
Genre: Aftercare, Alternate Universe- No Supernatural, Anal Fingering, Anal Sex, BDSM, Bondage, Cock Rings, Consensual Corporal Punishment, Dom!Castiel, Dom/sub relationship, Enthusiastic Consent, Established Relationship - Destiel, Exhibitionism, Impact Play, M/M, Oral Sex, Orgasm Delay, Rimming, Strapping, Sub!Dean, Team Dean's Red Ass, Threesome - M/M/M, Top!Benny, Top!Castiel, bottom!Dean, face fucking, pain play, switch!Benny
Language: English
Status: Completed
Published: 2016-04-10
Updated: 2016-04-10
Packaged: 2018-06-01 12:02:58
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 13,519
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6518575
Author URL: https://archiveofourown.org/users/Dangerousnotbroken/pseuds/Dangerousnotbroken
Summary: <blockquote class="userstuff">
              <p>“Did you ever sleep with Benny? Before we met?”<br/>The question caught Dean off guard. It certainly didn’t feel like an accusation, and in any case, Dean hadn’t, but it was such a random inquiry. He couldn’t figure out Cas’ sudden interest in the subject and his confusion had him floundering for a moment before he responded.<br/>“Naw Cas. I mean, he’s a good lookin’ guy, but we never hooked up.” That settled, Dean nuzzled his face into the pillow, intent on drifting off to sleep.<br/>It was not to be.  It seemed Cas wasn’t done with him quite yet.<br/>“But you’ve thought about it.” Cas didn’t even make it a question, just a statement of fact, waiting to be confirmed by Dean’s reply.</p>
            </blockquote>





	Our Boy Tonight

The roughness of fragrant hemp sliding gently across his fevered skin served only to ground Dean in the moment, bringing his consciousness back around little by little. He still drifted in the haze of subspace, content and happy and blissfully sore, but that subtle scratch was enough to allow little tendrils of reality back through. Dean didn’t fight the encroaching wakefulness but neither did he struggle to hasten its return. He just let it be, too peaceful to worry about the loss of that beautiful headspace or the realities of the world that would sink back in when he fully came back to himself. Castiel hummed softly above him as he worked to free Dean from the knots that had held him so securely through their scene. The part of Dean’s brain that clung to conscious thought recognized that Cas always kept a point of contact as he moved. A finger here, a hand there, a sweet and gentle touch of his lips when the rope pulled away and left bare skin exposed to the air again. The hum came again, only this time Dean recognized it as a noise of his own making.

“Hey there.” Cas’ softly murmuring voice always soothed Dean in these moments. Today was no exception. “How do you feel?”

“Super,” Dean replied groggily. The mattress beneath him, soft and supple despite how well it supported his weight, yielded and shifted as he tried to push up to hands and knees. Cas forestalled his motion with a hand on the small of his back.

“Take your time,” he insisted. “There’s no rush. You can stay right here as long as you need to.” Dean relaxed back into the comforting support of the bed with a heavy but pleased sigh, letting Cas’ touches soothe and calm him. The gentle touches sweeping across his skin were so markedly different than the touches that led them in to the evening’s scene. Where before Cas was all aggression and ferocity, fingertips pressing so firmly into Dean’s skin that he was shocked not to see bruises blossom in their wake, these touches were soft and tender, caresses so light they merely suggested contact.

Dean loved the aggression. He loved the rough grip, the sense of being claimed. He loved the way Castiel manhandled him and restrained him and took him apart, but he loved the reverent way Castiel touched him in the aftermath nearly as much. He’d never be able to give up either of them, and he could never have one without the other.

Later, when Dean trusted his legs enough to stand, Cas led him to the bathroom and ran the shower. The water was cooler than Dean would have chosen if he were asked.

Castiel did not ask.

He knew full well that Dean preferred scalding hot showers that steamed the mirror and left him sweating. He also knew that water that hot would be unpleasant on the freshly striped skin of Dean’s ass, and that Dean would bear the pain just to revel in the warmth if the decision was left up to him. That’s why, in his infinite wisdom, he kept the decision well out of Dean’s hands. Still, the water was warm enough not to leave a chill in Dean’s bones and Cas’ hands trailing fragrant soap across his tired muscles soon made him forget all about the inadequate water temperature.

When Cas let Dean crawl back into bed, scrubbed and relaxed, calm and sleepy, Cas climbed in right behind him, wrapping Dean up in his strong arms and pressing soft kisses to the back of his neck. Normally on nights like this they cuddled quietly until sleep claimed them. This time, Cas’ voice broke through the darkness.

“Did you ever sleep with Benny? Before we met?”

The question caught Dean off guard. It certainly didn’t feel like an accusation, and in any case, Dean hadn’t, but it was such a random inquiry. He couldn’t figure out Cas’ sudden interest in the subject and his confusion had him floundering for a moment before he responded.

“Naw Cas. I mean, he’s a good lookin’ guy, but we never hooked up.” That settled, Dean nuzzled his face into the pillow, intent on drifting off to sleep.

It was not to be.  It seemed Cas wasn’t done with him quite yet.

“But you’ve thought about it.” Cas didn’t even make it a question, just a statement of fact, waiting to be confirmed by Dean’s reply.

“Well sure. But he’s my roommate. It’d be weird.”

“For you, or for him?”

Dean pondered the question for a moment, the gentle sounds of their breathing the only intrusion on the silence of the darkened room. “Him, probably. I think if we’d hooked up I’d be cool with things the way they are. Benny might not though. Why the Spanish Inquisition?”

“Just curious,” Cas told him. If Dean were less sleepy he might have pushed harder. He _was_ sleepy though, so he didn’t, and the conversation faltered. Moments later, Dean succumbed to the sweet allure of the sandman and thought no more of it.

That is to say, Dean thought no more on the subject until approximately three weeks later, when he came home from work to find Cas already in his living room. That in itself wasn’t exactly odd. Castiel had been in possession of a key to Dean’s home (and vice-versa) for quite some time now. He rarely came over unannounced though and while Dean couldn’t recall for certain, he didn’t think they had plans he was forgetting about, making Cas’ presence a bit unexpected.

“Hello, Dean,” Cas purred softly, vacating his seat on the couch to meet Dean in the doorway. Despite the grease on Dean’s knuckles and the sweat on his brow, Cas invaded his space and kissed him softly, sweetly.  It took Dean more than a few moments to remember to ask any questions.

“What gives?” he inquired casually when it finally occurred to him to do so. “Did we have something planned for tonight? I must have forgot to put it in my calendar. I’m so sorry.”

Cas shook his head. A clever smirk started to assert itself across his lips, quickly schooled to blankness by his enviable self-control. “You’re not forgetting anything,” Cas explained carefully. “This is…why don’t you come sit down and I’ll explain. I think you’ll forgive me for showing up unannounced once I’m done.” In contrast to his usual stoicism Castiel appeared more than a little apprehensive as he spoke, rushing the last of the words out as if trying to forestall any kind of protest Dean might put up. It was only then that Dean noticed Benny seated in the living room, taking his ease in the well-worn armchair in the corner, broad arms crossed over his broader chest. He greeted Dean with an amiable nod of his head but offered no comment on the subject, only serving to deepen Dean’s curiosity.

“Benny and I have been speaking.” Castiel offered up this up like an admission, but it was not an especially shocking piece of information. Although they only met via their respective connections to Dean, Cas and Benny had always been friendly. He’d never known them to spend any time together without him, but it would neither have surprised nor bothered him if they had.

“About anything specific or…?” Dean let the remainder of the question hang unspoken, dropping on to the couch heavily. He really needed a shower. There was brake dust under his fingernails and he couldn’t imagine he smelled particularly appealing at the moment.

“About you actually,” Benny offered, then shot Cas an apologetic look. Ok, so there was a plan for this conversation, and Benny had clearly just deviated from the agreed-upon strategy. Now the gears in Dean’s brain started to turn.

“What Benny and I have been talking about,” Cas continued, unperturbed, “is the fact that despite your very clear attraction to each other, the two of you have never ended up in bed together. Personally, I think this is a crying shame.”

Dean, stunned, let his gaze bounce back and forth between his lover and his friend, unsure if he trusted himself to speak on the subject. Neither face showed any hint of joke or lie.

Dean still didn’t understand.

Cas took pity on him then, resting a gentle palm on the back of Dean’s hand, offering him a touch to ground himself before speaking again. “After our conversation a few weeks ago when I asked if you had ever hooked up, I spent some time observing the two of you a bit more carefully. I know unresolved sexual tension when I see it. So I approached Benny on the subject. And we agreed, if you’re amenable, that Benny should come play with us.”

This time, Dean found himself perfectly capable of speaking. “You planned a three-way with my roommate?” He wasn’t sure if he meant to sound indignant, thrilled, or both, and he was even less sure which one he managed to convey with his words.

“Only if you like the idea,” Benny interjected quickly. “I mean, your boy surprised me with the notion at first, but he talks sense. Could be fun.” Even though Benny spoke with his usual nonchalance, Dean could catch a hint of anticipation simmering below the surface, a tiny fear that he’d been party to something that was going to cause a rift between himself and the friend he’d lived with for years.

Sensing that Dean wasn’t ready comment further yet, Cas barrelled on. “I haven’t shared any details about your preferences, but we did discuss Benny’s and I can confirm that nothing he’s into falls in either your yellow or red zone. We can discuss the specifics in more detail if you decide you’re on board. What do you think?”

“I…” Dean began before faltering. “Benny, can you give us a minute to talk about it? It’s not no. I just…” He shrugged, letting the gesture speak for him.

“Say no more, brother,” Benny told him jeasily. Dean waited for his heavy footsteps to recede down the carpeted hallway of their small, rented house before speaking again.

“Why?” He managed to say a lot with that single word, knowing Cas would hear all the various incarnations of the question.

“Same reason I do anything I do when we scene. I want to take you apart and see what makes you tick. I want to make you feel so good you think you’ll never feel that good again, and then I want to make you feel even better. I want to give you everything your little heart desires and I think your heart desires this.” Cas smiled, not the warm and disarming smile Dean expected but a devious, sinful little thing that served to spark a flame in Dean’s blood. “And, if I’m being honest, I think the sight of those big hands all over you…” He laughed darkly, the kind of laugh Dean was used to hearing when his hands were bound and his ass about to serve as canvas for a strap or a paddle or Cas’ bare hand. “I’d be lying if I said this wasn’t a little bit of a fantasy of mine. You can say no though. I won’t be upset. Benny won’t be upset.”

“And what happens if I say yes?” It didn’t matter that Dean phrased it as a hypothetical. The rush of blood that coloured his face said more than enough about his thoughts on the matter, and Cas knew how to read Dean better than anyone.

“Haven’t really settled that yet,” Cas replied with a casual shrug of his shoulders. “I figured I’d give you the option of being involved in that conversation if you wanted this. Or if you’d rather be surprised, you could go take the shower you’ve been thinking about since you got home, and I can negotiate with Benny on your behalf.”

“You make it sound like a fuckin’ business deal,” Dean scoffed.

“A scene is always a negotiation, Dean. You know that. It doesn’t change just because there’s a third person involved. So. Do you need some time to think about it?”

Dean could easily have said he did. He could have taken the evening, or the day, or as long as he wanted to mull the idea over. He could have come up with a whole host of reasons why it was a bad idea, force himself to weigh the pros and cons and really get into the analysis of the thing before giving an answer. But really, what would the point be? He knew right away what his answer would be. It wasn’t even a question. Dean was emphatically, enthusiastically, irrevocably on the side of yes. He just needed to conjure up the stones to actually _say_ it. The quiet was nearly oppressive while he sat beside Cas and tried to summon the fortitude to accept this glorious gift he was being offered.

“How did I get so lucky?” Dean asked finally, grinning broadly at his boyfriend. “I do kinda want the surprise though, if that’s ok with you?”

“Oh Dean,” Cas replied with a devious kind of mirth in his tone. “You know how much I love surprises.”

The entire time Dean stood in the shower, this time nearly scalding hot as there were no welts on his ass to contend with, he let his mind race. What would Cas and Benny plan for him? Cas knew how to push all Dean’s buttons at this point. He knew what to do to tease him, how to get him off quick, and what would have him begging. The idea of having another person there while Cas wielded all this knowledge gave Dean such a thrill. He’d be lying if he said he hadn’t thought about it before. Benny was…fuck. Hands big enough to pin Dean’s wrists easily, those strong, broad shoulders and that mouth!

Yeah, of course Dean had given thought to what it would be like to get in bed with the guy. But that had been a long time ago, back before he met Cas, and once that happened there wasn’t really any need to fantasize anymore. Cas seemed to make it his personal mission to satisfy every single one of Dean’s desires (even ones Dean himself hadn’t been aware of) so daydreaming about his roommate had no longer seemed a necessary distraction. Still, even knowing that he and Cas had talked in the past about the vague idea of introducing a third party into their play, this was unexpected. Cas had sounded a lot more like he was asking if it was something that Dean wanted rather than actually requesting to do so and anyway, that had been months ago. It had been a short enough conversation and enough time had passed since that Dean had largely forgotten about it until today. But ok, yes, he did tell Cas that he’d be interested in doing so if the right person and the right scenario presented themselves. He just never figured the right person would be quite so…close to home.

The way the house was laid out, Dean had no option but to walk past the living room on his way back to his bedroom to dress.  He was clad only in a towel, the result of possessing insufficient foresight to bring a change of clothes in to the bathroom with him.  The way Cas’ eyes raked over his body in the brief moment before he could duck into his room was expected and familiar, but the feel of Benny’s eyes on his skin was wholly new. Startling. Thrilling.

The hunger on his features as he stared at Dean, permitted for the first time to look freely—well, it just served to solidify Dean’s decision in his mind, but he refrained from commenting for the moment. Instead, he dressed as quickly as he dared before rejoining the other two men in the living room.

“You put on clothes.” Castiel pointed out the obvious with no small note of disappointment, frowning at Dean as he entered the room. Benny still occupied the armchair, his large frame dominating the thing. Each held a bottle of beer in their hands. When Dean took his seat on the couch beside Cas he was handed his own drink, an ice cold bottle with condensation dripping down the glass.

Dean raised an eyebrow. “Well, you know, I thought we’d probably end up eating dinner before this thing happens, and that seemed like a pants occasion.” He spoke the words casually but let the look he gave Cas do the real talking. _If you wanted me naked, you should have given me an order,_ his smirk said. The narrowing of Cas’ eyes told Dean he was received loud and clear. Dean knew he might pay for that later and honestly, he wasn’t sure he’d be upset about it.

Instead of issuing such an order, Cas just took a sip of his beer and rested his free hand on Dean’s knee, giving him a gentle squeeze that was actually quite reassuring. It seemed that Cas was feeling more permissive than usual this evening. Any other night he would have made some very pointed comment about Dean’s smart mouth, and would all but confirm that there would be a reckoning later when they were alone. Ostensibly, bringing Benny to the party was for Dean’s benefit, but the more he thought about it, the more Dean was forced to acknowledge that Cas might be just as excited about it. The idea seemed to be pushing some buttons Dean couldn’t quite identify. He still had no idea exactly what he was getting himself into, but it was certain to be well worth the anticipation.

Unsurprisingly, since Dean had given Cas permission to keep the plans for the evening a secret, he guarded the details closely. The entire time they waited for the pizza Benny had ordered while Dean had his shower Castiel carefully kept the conversation on neutral subjects. Work. Local sports teams. Movies. He didn’t volunteer even a hint of what he and Benny had agreed to. Aside from a reasonable expectation that he was getting fucked, Dean was granted not a single clue as to what to expect.

Maybe half an hour after they finished dinner, Castiel stood up abruptly and left the room without so much as a word of explanation. Dean thought he caught the slightest hint of a nod exchanged between his boyfriend and his roommate, but he only had a second or two to process before the space Cas had recently vacated on the couch was occupied again, this time by the burly Cajun who had only moments before been half way across the room. Dean opened his mouth to say something, though he never got around to deciding exactly what.

Instead, he found himself being kissed quite soundly.  Benny’s rough fingers cradled his jaw, tilting his face up to meet just the right angle, and all other thoughts quickly fled Dean’s brain. All he could think about was the fierce way Benny kissed, the way his beard felt so different against Dean’s skin than Cas’ clean-shaven jaw did. It was just a kiss but it managed to nearly steal Dean’s breath straight out of his lungs, and by the time they broke apart Dean was dizzy from it. When his eyes focused again he took in the look on Benny’s face, a thoroughly satisfied and crooked grin, and followed his gaze to discover that it wasn’t Dean he was smirking at.

Dean turned slowly in his seat to find Cas, returned from whatever errand had taken him from the room in the first place, leaning against the doorframe with arms crossed over his chest and a glint in his ice blue eyes that could only be described as wicked. He nodded sharply at Benny, but didn’t appear to have any designs on moving from his vantage point across the room.

This apparently was the signal Benny was waiting for. Whereas the first kiss had been fierce but clearly exploratory, testing the waters and getting a feel for how Dean responded to his touch, this second kiss was a call to action. As soon as their mouths met one of Benny’s hands found its way to the back of Dean’s head and the other to his waist, pulling Dean in like his only thought in the world was to get them as close together as possible. If Dean had any designs on taking this thing slow he’d have been forced to alter his plan in that moment. He didn’t, of course. He had no plans whatsoever, but if he had, Benny would have changed them.

Somewhere in the back of Dean’s mind, he vaguely recognized that the shift in weight on the couch beside him was concrete evidence that Cas had crossed the room and sat down at his back, but it didn’t really register until he felt a second pair of hands on his body. Cas danced his fingers under the hem of Dean’s shirt and smoothed them around to splay across Dean’s belly. Now that he was certain of the presence of his (totally wonderful and completely amazing) boyfriend, Dean attempted to break away from the kiss to tell Cas exactly how awesome he thought this entire thing was. Benny’s hands held him fast though, and Cas slid one of his hands up to tease Dean’s nipple beneath his shirt as he spoke.

“Did you know Benny is a switch?” There was no answer available to Dean. He couldn’t speak with his mouth so engaged and he couldn’t shake his head without likewise breaking the kiss. Cas didn’t actually appear to expect an answer, thankfully. “I don’t believe the two of you have ever had the opportunity to discuss your interests,” he continued, “but let me tell you my love, you’re quite compatible. I don’t want to give too much away though. I know you like surprises.” In response to the soft voice murmuring in his ear, Dean let out a tiny moan against Benny’s mouth.

“I think you’ll like what we have planned for you,” Cas assured Dean. While there was little doubt in Dean’s mind that this would be true, the words still gave him a thrill. Instead of detailing exactly what these plans were, Castiel dipped his head down to press hot kisses along Dean’s neck. When his lips reached Dean’s jaw, Benny saw fit to loosen his hold on Dean’s hair and relinquish his mouth.  No sooner had Dean drawn a full breath than he found himself claimed again. This time it was Cas kissing him passionately, licking into his mouth and biting at his bottom lip. For a brief moment, the only reminder Dean had that there was a third person in the room was the fact that he still clung to Benny’s shirt with both hands. That is, until Benny’s hand, the one that had been holding Dean by the hip, found its way around to palm at Dean’s cock through his jeans. Dean let out a pleased groan, earning a low rumble of a laugh from Benny.

“Fuck, you’re hard already,” Benny murmured. “And we’re just getting started.”

“You think we should move this to the bedroom?” Cas asked. He sounded much calmer than Dean felt at that exact moment, cool and collected like he always did.

“Your call,” Benny told him plainly. The heel of his hand pressed firmly into Dean’s crotch and when Dean took it upon himself to turn his head just slightly, bringing Benny back into his field of view, the Cajun’s eyes were dark with lust.

Cas’ answer was to stand abruptly, sliding his hands out from under Dean’s shirt in one fluid motion. “Bring him,” he told Benny, striding quickly out of the room and down the hallway. Benny watched him leave before he stood, adjusting himself in his jeans and motioning for Dean to follow.

Dean expected to be led to his own room. It seemed obvious. That was always where he and Cas scened unless they were at Cas’ place. Instead, he was led into Benny’s room, lit with lamps in the corners so that shadows danced over every surface. Dean had seen the inside of Benny’s room before, obviously, but he’d never had cause to spend much time in there.  Although he was still in a safe place, in his home, it made the whole thing feel somewhat strange. He was forced to assume that this was part of the plan. Castiel had a way of planning things out right down to this kind of detail.

There were a few toys on the bed, a paddle and a strap that Dean recognized as Cas’ and a set of restraints that Dean didn’t mark as familiar. A bottle of lube sat proudly on the nightstand. Cas sat in a chair in one corner, his commanding posture giving him a regal air as he surveyed the two men entering the room.

“Come here, Dean,” he commanded, knowing full well that Dean would jump to obey. Dean approached his boyfriend quickly, sinking to his knees at Cas’ feet when Cas snapped his fingers sharply and pointed downward. Cas reached out and ran his fingers gently through Dean’s hair. “Good boy,” he crooned softly. “What’s your colour?”

“Green, sir,” Dean replied quickly, leaning unconsciously into Cas’ touch. The feeling of Cas’ nails dragging against his scalp was so soothing, so calming. Any apprehension he had about the events that were about to unfold just seemed to melt away.

“Excellent,” Cas replied. “Do you want to know what we’re going to do with you? I want to keep you guessing but if that makes you uncomfortable we can discuss it further.”

Dean shook his head. “No sir. I trust you.” Cas grinned broadly, a mix of satisfaction and wickedness.

“My good boy. I will not betray that trust. If you change your mind at any point, you just give me your colour and it stops. You remember who is really in control here?”

Dean nodded his understanding. This was Cas’ basic rule, driven into Dean with relentless determination since their first scene together. No matter what they did, no matter how far things went, Dean was always in control. Anyone who didn’t understand their relationship might say that was a deception, but Dean and Cas understood the truth.

Castiel held all the power in the moment. He could hurt Dean or give him great pleasure on a whim, he could grant rewards and give punishments, whatever he wanted to do, and Dean would go along with it. But the power was only in Cas’ hands because Dean gave it freely and of his own volition, and the second he chose to take it back everything would stop. Cas could do anything he wanted, _make_ Dean do whatever he wanted, but it was only because Dean permitted him this power. All it would take was one single word and everything else would fall away. Castiel was the one who wielded all the power but it was Dean who owned it.

There had only been a couple of times in past where Dean had needed to exercise that right. None had been because of a lack of care on Cas’ part, just bad moments where all the elements conspired to put Dean into the exact wrong headspace and push him to his emotional limits.  More than anything, Cas had been proud of him for knowing himself well enough to call a stop to things. It had only served to deepen the trust they had in each other.

Cas accepted Dean’s nod, tilting his head up to take Benny into his gaze as well. His voice grew louder when he spoke again. “For the moment, I think I am content to observe. I want to see how well you boys play together. Dean, you will obey all of Benny’s commands as if they were my own but you will both obey my word. Benny, what is your colour?”

“Green, sir.” It was so odd to hear Benny like this, at once commanding and deferential. Dean was fairly certain he was going to grow to like this side of his friend.

“Very well. You may begin.” Cas untangled his fingers from the hair atop Dean’s head and rested both his hands on the chair’s armrests. He looked like nothing so much as a king on his throne, posture strong and commanding, eyes dark and jaw set. Dean loved this look on him. His features always shifted just so when they went into a scene, revealing a side of him he never showed outside the bedroom.

“Dean,” Benny’s voice boomed, snapping Dean back to reality. “On your feet.” Dean obeyed with alacrity, standing quickly and crossing the room to take Benny’s outstretched hand. He pulled Dean close, grabbing his ass and putting his lips close enough to whisper in Dean’s ear. “I’m gonna have so much fun taking you apart,” he promised, sending shivers up Dean’s spine. “Your boy here told me _alI_ about what makes you tick. Can’t believe I’ve known you all these years and I had no idea what you were into. You gonna be a good boy for me, Dean?”

“Yes, sir,” Dean groaned hastily, nearly losing his footing when he found himself spun around to face Cas. Benny’s hands went right for the buttons on Dean’s shirt.

“Don’t close your eyes,” he commanded. “I want them on Cas the whole time I undress you. I want you to see how much he enjoys watching this. He was so disappointed when you got dressed after your shower earlier. I think we should make up for that, don’t you?” Even if it wasn’t in Dean’s nature to obey a command like that, he’d be hard pressed to do anything else.

Cas watched him from across the room with rapt attention, his eyes following the motions of Benny’s hands as they pushed the shirt from Dean’s shoulders and threw it on the floor. Those hands were warm when they made their way under Dean’s t-shirt, rough with calluses but gentle in their touch. Dean gasped as they moved upwards to pinch his nipples, applying firm pressure that was just this side of painful. His eyes wanted to flutter closed to allow him to focus on the sensations but he fought it, forcing them to stay open and trained on Cas. He watched Dean with such intensity, clearly enjoying the sight.

It was also obvious to Dean that a large part of Cas wanted to be the one with his hands all over Dean, making it a struggle for him to stay seated. Cas was always relentlessly dedicated to any plan he put in motion, so whatever he and Benny had agreed upon, Dean had no doubt that he would stick to it no matter how much he wanted to get his hands on Dean.

When Benny tugged Dean’s t-shirt up over his head and dropped it to the floor, he felt laid bare, more naked than if he were actually naked. Being exposed like this while Cas watched, it was…fuck, it was thrilling. Benny hadn’t even done anything yet, had barely touched him, but his cock strained at the zipper on his jeans and his breath came short and shallow and Cas just _sat there_ , implacably calm, and watched him fall apart piece by piece.

His belt buckle clattered and thick denim rustled loudly, and soon Dean found himself with his jeans in a pool around his ankles, only the thin cotton of his boxer briefs serving to contain his excitement. The corner of Cas’ mouth quirked upwards in the barest hint of a smile, but it said plenty. This is what Benny wanted. He wanted Dean to see the lust darken his boyfriend’s eyes as he watched Benny strip away all Dean’s clothes, leaving him naked and exposed. He wanted Dean to know how much it turned Cas on to watch him get manhandled like this. It wasn’t just about doing things to Dean, although Cas certainly did enjoy being the one to make Dean whimper. There was something about Dean’s pleasure that Cas found so intriguing that he didn’t even need to be directly involved to enjoy it.

There was no hesitation when Benny got his thumbs hooked into the waistband of Dean’s shorts. He tugged them down in one smooth motion and let them fall to the floor with Dean’s jeans.  Under his guidance, Dean stepped out of the pool of fabric and swiftly kicked it aside. He now stood totally exposed, nothing to hide behind, cock erect and leaking, with no idea what was coming next. Cas grinned and shifted in his seat, leaning forward slightly in anticipation.

Benny grabbed Dean’s hand, previously hanging useless at his side, guiding it to wrap around his own cock. He gave a few strokes with their hands in tandem before letting go. “Get yourself nice and hard for me, Dean. Stay right where you are, and don’t stop until I tell you.” Benny stepped back then, the warmth of his body retreating and leaving Dean with his hand on his cock, stroking himself slowly while Cas stared him down.

He’d never…Cas always wanted to touch him. He rarely had Dean touch himself during scenes. It wasn’t that he denied Dean his pleasure (except when he did on purpose, and ye gods was it good when Cas finally relented and let him come after all the waiting), but it was always Cas’ hand on his dick. There was something so much more exhibitionist about touching himself like this while Cas watched from a distance.

Part of him really wanted to put on a show. The other part, the part that won out, said that Benny told him to touch himself and stay right where he was. That left very little room for interpretation so other than the slow drag of his hand over his dick, Dean didn’t move.

It was only a sense of spatial awareness telling Dean that Benny was still standing somewhere behind him, for the Cajun made no sound as he stood watching Dean work, breaths quiet enough to escape notice as he stood nearly motionless. For a little while Dean almost forgot there was anyone else in the room until he heard Benny hum softly.

He stepped up right behind Dean, letting his hips press close, and Dean could feel the thick line of his cock through Benny’s jeans, pressing against the swell of his ass. He sent up a silent hope that part of the night’s plan was to let him get his mouth around that cock. It would be a shame if he didn’t get to. He might have to resort to begging.

Benny’s hand closed around Dean’s, squeezing tight and forcing a moan from his lips that he barely managed to stifle.  “Oh, don’t hold back. I wanna hear every sound you got for me,” Benny chastised, stroking Dean’s dick firmly. Dean moaned louder this time, unhindered. “Atta boy,” he praised, still with his hand wrapped around Dean’s. “What do you think Cas, is he hard enough yet? Or should we make him work for it a bit more?”

“He looks good from here,” Cas replied jovially, “but I think we need to make sure he stays that way, don’t you?” Benny’s dark chuckle was his only reply as he settled the cock ring snugly around the base of Dean’s cock without a word.

Fuck.

Dean was so, screwed. These two were going to be the death of him. He dropped his chin to his chest, already almost overwhelmed, and his eyes fell on the footlocker that normally sat at the foot of Benny’s bed. It had been dragged out into the center of the open part of the room and draped with a folded blanket.  In that moment Dean knew, he _knew_ he was going to end up bent over that footlocker before this night was over.

He was distracted from thinking on the matter further when Benny dangled the restraints that had previously occupied a corner of the bed in front of his face. “What’s your color?” he asked firmly, shaking the restraints and letting the leather and metal clatter in Dean’s field of vision to make it clear what the subject of his question was.

“Green,” Dean told him confidently. “ _So_ green.” There might have been a time that Dean felt ashamed of how much he loved being tied up and manhandled but it had passed long, _long_ before this evening, and he was in no mood to deny how excited he was at the prospect of Benny strapping him into those cuffs.

“Good boy,” Benny told him. The Cajun couldn’t see the delight on Dean’s face in response to the praise but Cas could, and he looked nearly as pleased as Dean did. Benny sank to his knees to one side of Dean and began to fasten one of the cuffs around his thigh, adjusting it carefully until it sat just right, tight enough to stay still but not to cause Dean undue discomfort. Then he attached the padded cuff on the other end of the short chain to Dean’s wrist, checking the tightness.

Dean was afforded only a slight range of motion. He could move his hands maybe six inches away from his thighs but that was about it, and the buckles sat in such a position that he would have a very difficult time releasing himself, if he were so inclined. It also meant that there was no way he was touching his own cock again unless one of his partners saw fit to release him—not that it mattered, because with the cock ring on there was little chance of Dean making himself come whether his hands were free or not. They’d take care of him, though. Cas always did, and the fact that Benny had never had Dean at his mercy like this before didn’t change the fact that Dean trusted him.

Benny soon had his other side fastened in the second cuff set. He stood up and walked across the room to Cas’ side to survey his work.  “He looks good,” Cas mused softly. His words were meant for Benny but he spoke loudly enough that Dean could still hear him clearly. “He always looks so good when he’s bound.”

“I love the way he blushes,” Benny agreed. “Your boy is so responsive.”

Cas shook his head, laughing softly. “Tonight, he’s our boy. And yes, he’s very, very good. Aren’t you, Dean?” Dean felt his face heat in response to the praise and his hands twitched in their cuffs, fighting the urge to tug at them. He knew he wouldn’t be able to lift his hands high enough to hide behind but his limbs wanted to try anyway.

“Yes, sir,” he breathed out finally. Dean kept his posture as upright as he could make himself. Cas always liked it best when he displayed himself well. He assumed Benny would too.

“How many years have you known Benny?” Cas asked. “Five? Six?”

Dean thought for a moment. What year was it when he met Benny in that shitty dive bar? Sam had just headed off to college and Dean was lamenting the loss of a brother and a drinking buddy in the same person that weekend, so it must have been… “Seven years, sir. Nearly eight.”

“Eight years,” Cas repeated. “Eight years and you never let on any hint of how attracted you were to each other. My, my. What restraint. Just think what you missed out on by denying this for so long.” He turned to face Benny, still standing obediently at his side. “I think five per year ought to do, don’t you?”

Benny replied with a sharp nod. “Yes sir,” he drawled, stepping away from Cas to approach Dean.

“And Benny?” Cas interjected. The Cajun halted and turned on his heels. “You’re still wearing an awful lot of clothing. See to that, won’t you?” Benny stiffened then ducked his head, sufficiently chastened. Perhaps he and Cas had come to an agreement about honorifics earlier because he didn’t receive the reprimand for leaving out the _yes sir_ that would have been exacted from Dean in a similar scenario.

Benny began to shed his own clothing, and Dean couldn’t help but notice he moved much more quickly than he had when undressing Dean, removing each article with perfunctory haste. This wasn’t about the tease, it was just about getting naked.  Nevertheless, Dean still took the opportunity to stare openly the whole time.

He’d seen Benny shirtless before. They’d lived together for long enough that it was bound to happen eventually. He was not a guy who wore shorts though, so the sight of his bare thighs was new, and Dean had _definitely_ never laid eyes on Benny’s cock before tonight. When Benny finally stripped down to nothing, the sight of it made Dean’s mouth water. Like the rest of the man, Benny’s cock was thick, and it was long enough that Dean wasn’t sure he’d be able to take the whole thing in his mouth. He was willing to give it a try though, just to be certain.

“Thank you, Benny,” Cas called across the room. “That’s much better.” Dean looked back to find that Cas had discarded his tie, opened the first few buttons at the top of his shirt, and rolled his sleeves up to the elbows. He still sat with such regal grace that it would be easy to assume he was unaffected by the scene unfolding before him, but Dean knew better than to fall victim to such false assumptions. Cas’ eyes, dark with lust and heavy lidded, told the truth. He _loved_ what he was seeing.

Benny strode back over to stand behind Dean, his confidence not lessened by his nudity, and placed a hand on the small of Dean’s back. Dean allowed Benny to guide him forward until he stood just a pace away from the footlocker. The thigh cuffs allowed him to walk without too much difficulty, though he wouldn’t be able to move very fast if the urge struck him. This, of course, didn’t bother Dean, as he didn’t expect to want to be anywhere but here for the rest of the evening.

“Oh your knees,” Benny commanded, his voice a thick drawl. A hand on Dean’s shoulder guided him down but he went willingly, dropping to a kneel on the soft carpet. Instinct tried to bring Dean’s hands up to brace himself on the edge of the footlocker, but he was abruptly halted by the short range of the chains on the cuffs.

Benny’s hand stopped him from pitching forward too fast, but as soon as Dean found his balance Benny pushed again, and soon Dean was folded over the footlocker, resting heavily on his chest. He’d need help getting up again later but that seemed like a very distant problem. Right now all Dean had to concern himself with was being prepared for whatever it was Benny was about to give him forty of. If Dean lifted his head he’d have a perfect line of sight to Cas on his throne, supervising the proceedings with his watchful eye. Even without the visual confirmation he could feel the weight of Cas’ gaze settling heavily upon him.

It was clear that Benny meant the touch of his hand on Dean’s hip to be comforting, grounding, and Dean took it as such. He relaxed under the gentle point of contact, settling his body as comfortably as possible in his restricted position. The footlocker was of an appropriate height for Dean to be bent over at least, and any discomfort he might feel was not going to be from the apparatus he was laid out on.

“Your boy tells me you like the strap,” Benny began conversationally. “Says you like the paddle too, or a bare hand, but the strap’s what you really like. Told me I could give you a choice if I wanted but I don’t think I do want to. I think I already know what you’d choose. Am I right, Dean?” He lifted his hand off Dean’s hip and brought it down on his ass, not hard enough to sting but still firmly.

Dean managed to remain perfectly still as he replied. “Yes, sir.” Benny swatted his ass again.

“That’s what I thought. You will count,” Benny announced, more a statement of fact than a command. “And you better keep track because if you miss your count, you don’t get your reward. You ready?”

“Green,” Dean affirmed.

As soon as the word left his mouth the first blow fell. It landed so quickly that Dean flinched noticeably, but he didn’t miss his count.

“One,” he called out clearly, then “Two,” when the next one landed shortly afterwards. Benny was clearly just warming him up because, though the strokes landed quickly, they were nowhere near firm enough to turn his ass the shade of red Cas would want to see. Still, it sent a thrill through him because it _wasn’t_ Cas raining the blows down, it was Benny, and Cas was just sitting there, watching.

“Three,” he called, and “four,” and when he reached five, it landed so much harder than the others that the word came out as more of a yelp than anything else.

Benny gave Dean a soft _tsk,_ running his rough palm over the spots he’d just worked over with the strap. “You’re starting to flinch. Stay still for me like a good boy,” he warned, and then abruptly the warmth of his hand was gone, quickly replaced by the crack of leather on skin. Dean struggled to stay still while he counted out the strokes.

Now that Dean was warmed up, Benny appeared to feel licence to be rather heavy-handed with the strap and soon Dean’s ass began to sting quite smartly.

This was the place Dean thrived. Bound and restrained and at the mercy of one he could trust, it became so easy to let go of everything outside the moment and let the pain subsume him. Dean’s voice called out the count with remarkable steadiness and each crack of the strap on his ass and thighs brought him closer to floating in that perfect space where he was nothing and everything all at once. He heard his own mouth say _twenty-five_ and that sounded about right, but he wasn’t entirely certain. The only thing that stilled his doubts was the fact that Benny didn’t chastise him for losing count.

Presently, Dean became aware of a new sensation. There was a hand on his head, stroking gently through his hair and when he craned his neck to look up he found that Cas had vacated his seat and now knelt in front of Dean, looking quite pleased. In the same moment, the blows ceased to fall, allowing Dean to fully experience the heat and pain that spread across his skin.

“Look at you,” Castiel said with a sigh. “Taking the strap so well. I’m always amazed at how well you handle this kind of thing. Do you need a break, or can you keep going?”

“Keep going,” Dean groaned with certainty. “I can take it.”

Cas beamed at this, his smile spreading warmth through Dean as he dragged the pad of his thumb along the edge of Dean’s stubbled jaw. Dean leaned into the touch and tried to take the thumb between his lips, eager to show Cas how much he wanted this, the strapping and the bondage and whatever else they wanted to give him. Cas pulled his thumb away at the last second.

“Now Dean, how are you supposed to count out your strapping if you’ve got something in your mouth? You’ve got fifteen left. I expect you to be good for Benny.” He teased the pad of his thumb along Dean’s lower lip as he spoke, his tone firm enough to brook no nonsense but still clearly fond and affectionate.

Dean whined softly, struggling to keep still as Benny began once again applying the strap enthusiastically to Dean’s ass. Cas cupped his jaw and held his gaze while he called out _twenty-six, twenty-seven, twenty-eight,_ and then in the space before the next stroke came, Benny spoke.

“Maybe he’ll have an easier time being patient if you show him what he’s gonna get after.” Dean could practically hear the wry smile that must be plastered across Benny’s face as he spoke. It was probably the same one that he could see creep onto Cas’ face from his current vantage point.

“What do you think, Dean? Would it motivate you if I showed you what you can expect as a reward?” Benny didn’t wait for Dean to answer before raining down the next three strokes in quick succession, forcing Dean to call out the numbers before replying lest he ruin his chances of earning the reward at all.

“Please, yes,” he whimpered as the pain blossomed across his skin. “I’ll be good, just please!” Taking in the warning in the arch of Cas’ eyebrow, he quickly added, “…sir,” hoping that Cas subscribed to the theory of ‘better late than never.’

“Very well,” Cas agreed fondly, letting go of Dean’s face and standing up. Dean lamented the loss of his touch but only briefly, because as soon as Cas came to his feet he began unbuckling his belt and undoing the fastenings on his pants. Then Dean’s feelings on the subject became quite the opposite, and he was so focused on the rapid increase in the amount of Cas’ skin he was privy to that he nearly missed calling out the next number in time to satisfy Benny. The thirty-second stroke fell remarkably sharply as a reminder to keep his mind on the task at hand.

“You have eight left,” Cas reminded him gently, dropping his pants to the floor to reveal his erection, thick and hard and curving up towards his belly. “And if you take them like a good boy, you get to suck my cock while Benny preps you. You’d like that, wouldn’t you?” he asked as if he didn’t know the answer perfectly well already.

“Good,” Cas continued, taking Dean’s groan as agreement, which was fair because it definitely was. “Benny, you may continue.” Cas sank back down to his knees on the carpet, one hand stroking his cock slowly and the other grabbing a handful of Dean’s hair to hold him steady. He kept his cock just out of Dean’s reach. If he craned his neck and stuck his tongue out as far as he could, he would still be just shy of reaching the bead of precome that sat at the head of that cock, teasing him with the promise of things to come.  Cas held him there with no inclination to mercy, not that Dean had expected any.

“Thirty-three,” Dean volunteered breathlessly in time with the sting of leather that landed over the lower curve of his ass. The very tip of the strap grazed ever-so-lightly over his balls as Benny pulled it away to line up for the next stroke, the mix of pleasure and pain sending a jolt through his body. The next few strokes landed on the fullest part of his ass, adding their sting to the pain already living there. Benny worked so quickly through the remaining strokes that Dean could barely get the numbers out in time, and soon there was just one stroke left to go.

Just one more, and Dean would earn his reward. He’d been good. He’d taken each stroke of the strapping with grace and strength and he hadn’t missed a single number even though his partners had done everything in their power to make it difficult for him. He’d been so good, and as soon as the strap connected with his sore, red ass one more time he’d get to take Cas’ gorgeous cock in his mouth.

Just one more.

He braced himself for the impact, but for the space of several long moments, it didn’t come. Dean breathed in slowly, carefully, and let the air out in a long release almost like a sigh, waiting as patiently as he could bear.  Still, the stroke didn’t come. He fought the urge to squirm, resisted the desire to pull against Cas’ hold on his hair and crane his neck to see what was halting Benny’s motions, and it _still_ didn’t fall.

Dean was beginning to think he’d done something wrong, and he had nearly worked up the nerve to inquire on the subject when his ears caught the faint sound of Benny’s arm cutting through the air. It was the only warning he received before the fortieth stroke, the most remarkably hard strapping yet, fell across both cheeks and left such a sharp sting on his skin that Dean was certain he could feel the edges of the stripe clearly through the haze of other sensations flaring through his body. He cried out the number with enthusiasm, proud of himself for keeping count so well, and was still breathing hard when Cas twitched his hips forward, nudging the tip of his cock against Dean’s parted lips. He opened wide to take it in, working his tongue through the bitter taste of precome and letting Cas slide into his mouth.

“Good boy,” Cas cooed, fingers still holding tight in Dean’s hair. All his motions were slow and controlled, never giving Dean more than he could handle, never taking more than Dean was ready to give. He preened under the praise, working with lips and tongue to give Cas as much pleasure as he could. It would be easier if he could move, of course, but what he lacked in range of motion he could make up in enthusiasm, and he certainly planned to do so. Dean knew somewhere in the back of his mind that this wasn’t all he should be experiencing right now, but he was really enjoying the cock in his mouth, so he didn’t spare too much thought for it. It’s not like he could do anything except work his mouth and suck Cas’ cock anyway.  Whatever was going to happen would happen without his intervention.

Cas’ free hand stroked over Dean’s lips where they stretched around his cock, admiring how beautifully they enveloped him. “Squeeze Benny’s fingers if you need help,” Cas told him, and Dean felt Benny’s solid hand slide into his own where it sagged in the cuff, giving him a reassuring squeeze but otherwise holding quite loosely. Dean didn’t expect to require assistance and he knew Cas didn’t plan to give him any reason to need it either, but it always felt good to know that his needs were being planned for. Cas pushed his hips forward again, his cock nudging at the back of Dean’s throat, and it was at this exact moment that Benny spread his cheeks with the hand that wasn’t holding Dean’s and licked tentatively across Dean’s hole.

Even with his mouth full of cock, Dean’s moan was loud enough to fill the room. A few gentle, careful licks had Dean relaxing into the touch, sagging bonelessly onto the footlocker and letting himself be swept away in the tide of sensation. Benny teased him with the point of his tongue, lapped messily at his hole and nipped at the reddened skin of his cheeks, and Cas slowly fucked his mouth, and all Dean had to do was lie there and take it.

And god, did he want to take it.

He could come just like this, helpless and at the mercy of his two partners, if it weren’t for the thin strap of leather snapped around his cock holding his orgasm at bay. Even with that, Dean was fairly certain if this kept going long enough the overwhelming pleasure would win out and he’d still end up coming all over the blanket beneath him. He hadn’t actually been given permission to come, of course, so he hoped it wouldn’t come to that, but it was a very real possibility.

Dean lost all sense of time. It could have been mere seconds with Benny’s face buried in his ass, licking him open with relentless dedication, it could have been hours. All Dean knew for sure was that it felt _good_ and he didn’t want it to stop.

When the warmth of Benny’s mouth retreated, he whined out the only complaint he was capable of with Cas’ cock filling his mouth but was soon placated when the Cajun’s thick finger pressed carefully into the spit-slick furl of his hole, teasing and probing carefully. Dean let out a relieved sigh which, with his mouth full as it was, came out more like _hmmph_ , but the sentiment was clear nevertheless.

This was good, and Dean wanted it, and his feelings on the subject only improved when Benny’s tongue was added back into the mix. Through it all, Cas kept fucking his mouth, muttering dark praise about Dean’s tongue and his lips and what a good boy he was, and Benny kept fingering and licking him open, and Dean could do nothing but moan and writhe and let them. The scratch of Benny’s beard against his ass served only to inflame the sting left by the strap, adding pain to the dual assaults of pleasure, and before too long it neared the point of too much. Dean was seriously considering tapping out, squeezing Benny’s hand so he could warn his tormentors that he was going to come with or without permission if they didn’t stop.

Only a few moments before he would eventually have decided to exercise his out Benny backed off, giving his hole one last teasing lick, and then everything stopped. Cas backed away, leaving Dean’s jaw aching and his mouth empty, Benny gave his ass a squeeze and got to his feet, and Dean drew the first proper breath he’d been able to in god only knows how long, careless of the spit running down his jaw or the few stray tears that had slid from his eyes. Dean heard Benny moving around beside him before he saw his feet come into view, halting at Cas’ side.

“See what you get when you’re patient?” came Benny’s deep rumble. Dean nodded agreement. For this, he could be patient. He could wait so well if at the end it meant he got tied up and spanked and used like this.  Still, he couldn’t help but wonder how they’d use him next.

He wanted everything. Everything they had planned for him and more. He wanted pleasure and pain, he wanted to be driven right to the edge and pushed over. Maybe Cas would have Benny fuck him while he watched. Maybe they’d take turns. Dean groaned in spite of himself, trying to imagine what it would feel like to have Benny’s thick cock splitting him open, or to be kept like this, bent over this footlocker as they kept him guessing when they were going to switch. Maybe a blindfold so he would have no idea who was touching him when.

Oh. Oh god. What if this didn’t have to be a one-time thing?

“You’re squirming again.” Dean hadn’t even realized he was doing it, and while Cas hadn’t actually said _don’t_ , he might as well have. There would be no reason to point it out otherwise.

Dean fought to stay still, fought to be patient. He could be good if he really wanted to. Craning his neck up, Dean let his eyes climb the legs of his dual tormentors. Benny stood with his arms crossed loosely over his chest, smirking down at Dean with barely contained glee. Castiel was much more stoic, his face a blank mask as it often was in the middle of their scenes.

He watched Dean with unreadable eyes as he undid the last few buttons on his dress shirt and tossed it to the floor, then met Dean’s gaze for a moment before a slow smile crept across his lips. He turned to face Benny and began to trail his fingertips over the man’s chest. Leaning in very close, he whispered something in Benny’s ear that Dean couldn’t catch even a hint of before they laughed softly over the shared secret.

Benny kissed Cas then, the first kiss Dean had seen them share.  He would not have expected the sight to be particularly arousing but good god, did that turn Dean on. Benny and Cas had their hands all over each other, pawing at asses and pinching nipples, fingertips roaming over skin and tangling in hair. Dean wondered absently if Cas’ whispered words had been an order to kiss him or something more abstract. He could certainly be that demanding when he saw fit.

Dean followed the path of Cas’ hands as they explored Benny’s body, waiting with bated breath for the moment he finally began to move lower.  Cas was never more a tease than when he knew Dean wanted something, when he planned on giving it to him eventually but wanted the satisfaction of drawing it out. He could make the simplest things last forever just to watch Dean struggle to maintain his composure and once that composure was gone and Dean was a whimpering, begging mess, desperate for satisfaction and release, he always managed to find a new reserve that let him prolong things even further.

Dean couldn’t fathom how Cas could do it. He’d be helpless to keep his hands off Cas if their roles were reversed. Hell, even without their roles reversed he’d have a hard time keeping his hands off of naked Cas if he weren’t tightly bound in leather at the moment. Cas, on the other hand, clearly knew that Dean was seething with anticipation, so it was with incremental slowness that his hands finally found their way south to lavish attention on Benny’s cock. His mouth never parted from Benny’s long enough to let the sounds of pleasure drift from his lips, but Dean could still hear snippets of the soft grunts and moans that resulted. Dean knew Cas’ tricks well enough to tell that he wasn’t trying to get Benny off. It was simply too slow, the strokes too languid to be anything more than just the next phase of torment. His thumb barely grazed over the head on a few passes and he held his grip loose around the shaft. If Dean had to guess, he’d have said it was just as much for Benny’s torment as for Dean’s.

“You want this,” Cas inquired with quiet amusement, dragging his lips away from Benny’s and glancing over his shoulder at Dean, “don’t you?” He kept stroking Benny’s cock while he watched Dean, his face making it clear that he knew exactly what he was doing, exactly what the answer would be. All Dean could bring himself to do was nod, shaky at first, then with more enthusiasm. Castiel’s wry smile gave way to soft laughter before he turned his gaze back to Benny, pointing to a spot on the floor in front of Dean. A look passed between the two in the infinitesimal space between thought and motion, and before long Benny had repositioned himself in front of Dean and was sinking to kneel on the carpet. The position put his cock, fully erect and glistening slick in the low light, so close that Dean could almost taste it.

“I’m not done with it yet,” Cas told him, voice devoid of all empathy. He dropped to the floor in one fluid motion, bringing himself down to hands and knees and pushing Benny back to sit on his heels. Before Dean could register startled protest, his lips already parted in anticipation of the cock he thought he’d be sucking by now, Cas wrapped his own lips around that cock and swallowed it down mercilessly.

Between Benny’s startled gasp and Dean’s own disappointed whimper, it was truly a surprise that he could hear the quiet sounds Cas’ mouth made. The soft, wet noises were a treat all by themselves, and when added to the sight of Cas bobbing his head expertly as he worked his mouth around the impressive girth of Benny’s cock, it was hot enough that Dean was suddenly glad for the ring squeezing around the base of his cock. He chanced a quick glance upward, taking in the blissed-out look on Benny’s face while he tried valiantly to keep his arms at his sides.  Dean couldn’t decide whether to be jealous of Cas for having his mouth on Benny’s cock, or of Benny for having his dick between Cas’ talented lips.

By the time Cas pulled back, trailing the tip of his tongue along the underside of Benny’s cock, Dean had yet to determine which side of that line he fell on. He harboured a brief hope that it wouldn’t matter any longer because he’d get to have one of the two but Cas, ever the cruel taskmaster, instead turned his head to claim Dean’s lips in a languorous kiss. He could taste Benny on his lover’s tongue, just a hint of the bitter precome clinging to his mouth as Cas coaxed him to relax, drawing soft moans and tiny whimpers out with just the heat of his kiss. Then that mouth was gone and Cas was guiding Benny towards him, the ruddy head of his thick cock nudging at Dean’s lips as he opened to allow it entrance. He couldn’t contain the moan that emanated from deep in his throat, pleased beyond words to finally be tasting what he’d imagined. His lips strained around the girth, tongue working over the shaft as Cas decided arbitrarily how deep to let Dean take him. Dean could do nothing but take what he was given, nothing but lie there and let Cas guide Benny in, sometimes just the tip, sometimes nudging the back of his throat.

Abruptly, his lips had nothing stretching them open, no hot length stifling the desperate noises, and a shamefully loud moan drifted out. Cas dove in to fill the void with his tongue, licking into Dean’s mouth with fervor. Dean only had long enough to adjust to the shift before the kiss ended and he was treated to the tantalizing sight of Cas licking a fat stripe along Benny’s shaft. Benny’s hand twitched its way up from his side to grip Dean’s hair tight enough to pull at his scalp, then Cas guided Benny’s cock back into his mouth.

This became Dean’s torture. Every time his eyes came back into focus enough to appreciate the show that was playing out right in front of his face, he found his mouth full of cock, or Cas dragged his lip between teeth and worried it roughly before soothing it with his tongue. Every time he managed to sink into a rhythm kissing Cas or grew accustomed to the stretch of his lips around Benny’s cock, he found things shifting around him.

After a while, Dean stopped trying to anticipate the shift and just let himself relax and become pliable, giving himself over to Cas’ whims. He sagged against the footlocker, his head held aloft only by Benny’s hold on his hair. Dean did what he always did when things got really good.

He let himself submit.

So complete was his surrender that it took more than a few moments for Dean to notice that the constant shifting had stopped and Benny was slowly bucking into his mouth unhindered and without faltering. Cas sat back up on his heels to watch for a moment, stroking his thumb along the corner of Dean’s mouth where it stretched open around Benny’s shaft.  He made pleased sounds, cooing over what a good boy Dean was, how well he took Benny’s cock, how perfect he looked with his mouth full. The praise sent a swell of pride through Dean’s quivering body, eager to please his lover and his friend.

“So good,” Cas affirmed once more, stroking his hand along Dean’s flank as he moved around behind him, coming to rest between Dean’s legs. His knees nudged Dean’s sideways until he could fit comfortably between them. Cas’ touches were all gentle and light, a beautiful contrast to the rough treatment of the strapping and the way Benny was using his mouth so roughly all the while. When the contact of his fingertips ceased, Dean heard the faint rustling of the wrapping on a condom, and within moments, the blunt head of Cas’ cock nudged at his opening. Cas’ hand slipped into Dean’s as his dick slid into Dean’s ass.

Dean couldn’t very well voice his opinion with Benny’s cock stretching his lips open and repositioning himself to allow for commentary wasn’t an option, so the desperate sounds emanating from his throat would just have to serve notice as to how much he was enjoying himself. His cock twitched valiantly, leaking fat droplets of precome as he groaned around his mouthful of cock, and though he knew Cas offered his hand as alternative to the safeword he couldn’t speak, exercising that option was the furthest thing from Dean’s mind. If anything, after so long being teased and tormented and denied, finally having the girth of Cas’ cock spearing him open while Benny filled his mouth was a dream come true, the greatest reward he could have been offered for his evening’s good behavior.

Cas could have taken him hard and fast and Dean would never have protested. He probably even would have liked it, but the slow and measured pace Cas set was a glorious thing, serving to set his every nerve on fire with the delicious assault of pleasure. Cas’ other hand settled gently on his hip as he drew back and slid home, slow and even strokes filling Dean up over and over and over.

Benny stopped moving and held his ground, letting the momentum of Cas’ thrusts drive Dean forward to slide slick lips along his shaft. The wet drag of the Cajun’s cock in and out of Dean’s mouth matched pace with the tantalizing friction of Cas’ cock driving into his ass.  The pleasure of both was heightened by the stinging welts on his ass, pain brought back to life by Cas’ hips colliding with his abused skin, and Dean could not possibly be happier—unless, of course, he realized absently, one of them saw fit to free him from the confines of the cock ring and let him come, but Dean had no illusions about that happening before Cas decided it was time.

“Goddamn, Dean, the mouth on you,” Benny groaned breathlessly, fingers tightening in his hair. Dean wished he had his hands free so he could give Benny the attention he deserved. It was blissfully satisfying to have Benny fucking his face, that much was certain, but it would be so much better if he could do it properly. Even so, the attention he was able to pay to Benny’s cock was clearly satisfying the other man. The bitter taste of precome danced across his tongue constantly, and if the sounds he was making were any indication, Benny did not begrudge the lack of hands-on engagement. If anything, it only increased his pleasure because the only action available to Dean was escape, and he didn’t choose that.

Unsurprisingly, after the prolonged teasing, Cas did not require much stimulation before he was teetering on the precipice of his inevitable orgasm. Dean could feel the pace of his thrusts speed up, jostling him against the surface of the footlocker, and then abruptly Cas faltered, slamming against Dean’s ass once, twice, three times more. Cas was always quiet when he came, but his pleasure was obvious from the way he gripped Dean’s hip as he shuddered through the final thrusts.

“Benny, now,” Cas commanded harshly, his voice wrecked and strained as he backed away, leaving Dean empty and wanting. When Benny drew back and rose to his feet, he moved immediately to pull Dean off the footlocker and help him to his admittedly unsteady feet. Dean whined despite his aching jaw, lamenting the emptiness they both left, but let himself be manhandled towards the bed. Cas had already climbed up and knelt proudly at the head of the bed, the condom disposed of sometime in the interim when Dean was too preoccupied to notice. Dean would never understand how Cas managed to remain so stoic in the moments shortly after coming, but it was not a feat Dean himself ever hoped to replicate. As soon as Dean knelt on the bed Cas reached between his legs and released the snaps on the cock ring, bringing a sigh of relief to Dean’s red and swollen lips.

“You can come whenever you like,” Cas told him smoothly, petting Dean’s hair. Between them, Benny and Cas guided Dean to lie on his stomach, cock trapped between his body and the mattress.  He was momentarily disappointed when Cas unclipped his cuffs from the straps around his thighs. The chains were short though, and when Cas joined them together to bind his wrists, it gave Dean very little range of motion, securing his hands at the small of his back. Cas gripped the chains to hold him steady, draping Dean’s torso across his lap and running reverent fingertips across his heated skin, soothing Dean and settling him back in his headspace. He passed Benny a condom with one hand, never breaking contact with Dean with the other, and Dean took the few small moments left to him to prepare himself for the thing he’d been anticipating all night.

Benny breached him unhurriedly, content to savour every second of tight friction Dean’s willing body could provide. Even prepped and wet and freshly fucked, Dean’s ass was not used to the stretch of Benny’s thick cock. The initial push seemed to drag on forever, Benny’s hips inching forward with such incremental caution that Dean could scarce feel him moving. It was all just the stretch and the burn and the pleasure filling him up and splitting him open until he couldn’t imagine anything more intense. He moaned against Cas’ skin, fighting the urge to writhe and nearly failing, his desperate desire to goad Benny into breaking with caution and just fucking him into the mattress coming close to defeating his deep rooted desire to be _good._

“See how tight he is?” Cas addressed Benny casually, almost conversationally. His fingertips worked in calming circles over Dean’s back and shoulders as he spoke, as though he knew exactly how much his words would inflame the desire simmering just below the surface of Dean’s consciousness.

Benny grunted. “So fuckin’ tight,” he agreed. His big hands pawed roughly at Dean’s hips as he finally sank in the rest of the way, their bodies flush together. It stung, of course, the evidence of a sound strapping still living on his skin, but Dean reveled in every second of the pain. It seemed like an eternity that he held steady, waiting for Dean to give sign that he was ready for more. Permission came in the form of a high-pitched, needy whine, one Dean couldn’t have imagined coming from his own throat before he heard it made manifest.

Benny pulled his hips back, tilting his ass up into the air, and began to pull back. He still moved slowly but it was markedly faster than he’d sunk in, and as soon as he drew back to the point that just the fat head of his cock was nestled between Dean’s cheeks he surged forward, driving the air out of Dean’s lungs with the ferocity of his thrust. He drew back again, just a little quicker but no less solid when he thrust his cock back into Dean’s slick hole, and with each thrust that followed he quickened. Soon, none of the measured caution that had begun the endeavour remained, leaving Benny to move with fevered intensity that only increased with each passing moment. Dean’s breaths came in ragged gasps accompanied by a constant litany of punched out little moans and grunts, a sinful chorus that matched the pace of Benny’s thrusts.

Dean had next to no warning before his orgasm ripped through him. The friction of his own dick trapped between his belly and the bed coupled with the near-overwhelming sensation of Benny’s big cock fucking into him mercilessly and the searing pain of Benny’s hips colliding with his welted ass was more than enough to drive him over the edge. Cas made pleased humming noises the whole time stroking Dean’s hair and murmuring praise while his body shuddered through the aftershocks.  He sagged like a boneless thing, no desire to move even if either Benny or Cas had felt inclined to let him go, and still Benny kept fucking him hard and fast, never slowing until at last, he slammed home and froze, working through his release and rutting his hips against Dean’s ass in short, shallow thrusts. The sound he made, somewhere between a groan and a growl, struck Dean as so remarkably feral that even in his blissed-out haze, he registered a burning desire to hear those sounds again, over and over, and bear pride in knowing he was the cause.

Presently, Dean became aware of hands rolling him onto his side. The chains holding his hands at the small of his back were unclipped and the leather around his wrists and thighs worked free by the other two men. Cas pressed his lips to Dean’s skin wherever leather had touched, just as he always did, before he leaned down to kiss Dean, both of them breathless and languid in the moment.

“I’m going to go get a cloth and some juice,” Cas told him gently when they finally broke their kiss. “Do you feel comfortable staying here with Benny?”

Aftercare was a sacred thing, unchanged by the addition of a third party, but after the night’s events Dean couldn’t imagine a scenario where he wouldn’t feel wholly safe in Benny’s presence. He nodded as enthusiastically as his drowsy, foggy state would allow, and felt Benny settle in behind him on the bed, broad arms wrapping around his waist in a protective embrace.

Satisfied, Cas climbed off the bed and padded naked and barefoot from the room. The touch of Benny’s hands on Dean’s skin felt so soothing. He dragged a fingertip through the mess of come still clinging to Dean’s belly, laughing softly at the way Dean squirmed against him, and when the squirming brought their faces in close proximity, it felt like the easiest thing in the world to let Benny claim his lips in a soft and tender kiss.

They kissed with no motive, just enjoying the taste of each other’s lips and the feeling of their bodies pressed together.  This was how Cas found them when he came back, and Dean half-thought to feel sheepish until he took in the warm smile on Cas’ face, thoroughly unperturbed by the tender act he was witnessing. He cleaned the come and lube from Dean’s skin with care and attention, then held a straw to Dean’s lips and urged him to drink deeply. The sweetness of the juice exploded on his tongue, drawing attention to the thirst he’d previously been unaware of. When he’d had his fill, Cas settled in beside him, his body and Benny’s bracketing Dean in warmth and comfort. They touched him gently and reverently, palms and fingertips gliding across warm skin. Dean hovered on the edge of sleep, clinging to consciousness with relentless determination when a thought crossed his mind.

“Should…” he began, words faltering. “Should we go back to my room? Let you sleep?”

Benny laughed softly, smiling against Dean’s skin. “Don’t see why you gotta unless you want to. Bed’s big enough for three.”

No, Dean didn’t really want to. The warm embrace of two lovers was a marvelous comfort he didn’t want to have to give up any time soon. He settled in sleepily, only barely aware of the blanket Cas draped across the three of them. It might be awkward waking up in Benny’s bed in the morning, bracketed by his boyfriend and his roommate, but the prospect of a sleepy morning make-out session made any potential awkwardness seem more than worth it.

Dean’s last waking thought was that he’d need to make them both breakfast in the morning. A night like the one he’d just been gifted with deserved a very tangible show of gratitude, and who knew?  If he played his cards right, they might just see fit to let it happen again.

**Author's Note:**

> I give the highest of praises to the lovely [KreweOfImp](http://archiveofourown.org/users/KreweOfImp) for beta reading this fic, screaming at me over some particularly choice phrasing, and giving me the push I needed to crank out this piece of filth.
> 
> If you're so inclined, I'm on [Tumblr ](http://shennanigoats.tumblr.com) and I'd love for you to come scream at me.


End file.
